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Winter Park is home to a plethora of world-class museums, high-end boutiques, some of the area's finest restaurants, and is centrally located being only minutes from downtown Orlando. Use our custom search tool to view all homes for sale under $400k in Winter Park or click here to return to the list of surrounding towns and cities in the Orlando area. Have questions? Contact us here.


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  1. Photo of 851 Miles Avenue #15, Winter Park, FL 32789 (MLS # O6257241)
    $245,000
    Photo of 851 Miles Avenue #15, Winter Park, FL 32789 (MLS # O6257241)
    Photo of 851 Miles Avenue #15, Winter Park, FL 32789 (MLS # O6257241)
    851 Miles Avenue #15, Winter Park, FL
    851 Miles Avenue #15
    Winter Park, FL
    • 2 Beds
    • 1 Bath
    • 808 Home (sqft)
    • 1 Bath
    • 1.05 Lot (ac)
  2. Photo of 432 W Swoope Avenue, Winter Park, FL 32789 (MLS # O6257130)
    $725,000
    Photo of 432 W Swoope Avenue, Winter Park, FL 32789 (MLS # O6257130)
    Photo of 432 W Swoope Avenue, Winter Park, FL 32789 (MLS # O6257130)
    432 W Swoope Avenue, Winter Park, FL
    432 W Swoope Avenue
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 2,317 Home (sqft)
    • 4 Baths
    • 872 Lot (sqft)
  3. Photo of 1757 Chilean Lane, Winter Park, FL 32792 (MLS # O6256824)
    $400,000
    Photo of 1757 Chilean Lane, Winter Park, FL 32792 (MLS # O6256824)
    Photo of 1757 Chilean Lane, Winter Park, FL 32792 (MLS # O6256824)
    1757 Chilean Lane, Winter Park, FL
    1757 Chilean Lane
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,413 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  4. Photo of 3651 N Goldenrod Road #208E, Winter Park, FL 32792 (MLS # O6256664)
    $195,000
    Photo of 3651 N Goldenrod Road #208E, Winter Park, FL 32792 (MLS # O6256664)
    Photo of 3651 N Goldenrod Road #208E, Winter Park, FL 32792 (MLS # O6256664)
    3651 N Goldenrod Road #208E, Winter Park, FL
    3651 N Goldenrod Road #208E
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 840 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  5. Photo of 2341 Devon Court, Winter Park, FL 32789 (MLS # O6257142)
    $499,000
    Photo of 2341 Devon Court, Winter Park, FL 32789 (MLS # O6257142)
    Photo of 2341 Devon Court, Winter Park, FL 32789 (MLS # O6257142)
    2341 Devon Court, Winter Park, FL
    2341 Devon Court
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,773 Home (sqft)
    • 2 Baths
    • 13,940 Lot (sqft)
  6. Photo of 3053 George Mason Avenue #8, Winter Park, FL 32792 (MLS # O6256375)
    $164,900
    Photo of 3053 George Mason Avenue #8, Winter Park, FL 32792 (MLS # O6256375)
    Photo of 3053 George Mason Avenue #8, Winter Park, FL 32792 (MLS # O6256375)
    21
     
    3053 George Mason Avenue #8, Winter Park, FL
    3053 George Mason Avenue #8
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,030 Home (sqft)
    • 2 Baths
    • 10.07 Lot (ac)
  7. Photo of 2494 Timberline Drive #2494, Winter Park, FL 32792 (MLS # O6251296)
    $250,000
    Photo of 2494 Timberline Drive #2494, Winter Park, FL 32792 (MLS # O6251296)
    Photo of 2494 Timberline Drive #2494, Winter Park, FL 32792 (MLS # O6251296)
    2494 Timberline Drive #2494, Winter Park, FL
    2494 Timberline Drive #2494
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,316 Home (sqft)
    • 2 Baths
    • 2,614 Lot (sqft)
  8. Photo of 3092 Nicholson Drive, Winter Park, FL 32792 (MLS # O6255970)
    $434,000
    Photo of 3092 Nicholson Drive, Winter Park, FL 32792 (MLS # O6255970)
    Photo of 3092 Nicholson Drive, Winter Park, FL 32792 (MLS # O6255970)
    3092 Nicholson Drive, Winter Park, FL
    3092 Nicholson Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,738 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  9. Photo of 535 N Interlachen Avenue #304, Winter Park, FL 32789 (MLS # O6256275)
    $395,000
    Photo of 535 N Interlachen Avenue #304, Winter Park, FL 32789 (MLS # O6256275)
    Photo of 535 N Interlachen Avenue #304, Winter Park, FL 32789 (MLS # O6256275)
    19
     
    535 N Interlachen Avenue #304, Winter Park, FL
    535 N Interlachen Avenue #304
    Winter Park, FL
    • 1 Bed
    • 2 Baths
    • 726 Home (sqft)
    • 2 Baths
    • 26,572 Lot (sqft)
  10. Photo of 1712 Bomi Circle, Winter Park, FL 32792 (MLS # O6256132)
    $579,000
    Photo of 1712 Bomi Circle, Winter Park, FL 32792 (MLS # O6256132)
    Photo of 1712 Bomi Circle, Winter Park, FL 32792 (MLS # O6256132)
    1712 Bomi Circle, Winter Park, FL
    1712 Bomi Circle
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 2,012 Home (sqft)
    • 2 Baths
    • 20,909 Lot (sqft)
  11. Photo of 101 S New York Ave #302, Winter Park, FL 32789 (MLS # O6256094)
    $1,695,000
    Photo of 101 S New York Ave #302, Winter Park, FL 32789 (MLS # O6256094)
    Photo of 101 S New York Ave #302, Winter Park, FL 32789 (MLS # O6256094)
    101 S New York Ave #302, Winter Park, FL
    101 S New York Ave #302
    Winter Park, FL
    • 3 Beds
    • 4 Baths
    • 3,174 Home (sqft)
    • 4 Baths
    • 20,038 Lot (sqft)
  12. Photo of 1751 Glencoe Road, Winter Park, FL 32789 (MLS # O6255877)
    $4,100,000
    Photo of 1751 Glencoe Road, Winter Park, FL 32789 (MLS # O6255877)
    Photo of 1751 Glencoe Road, Winter Park, FL 32789 (MLS # O6255877)
    1751 Glencoe Road, Winter Park, FL
    1751 Glencoe Road
    Winter Park, FL
    • 5 Beds
    • 6 Baths
    • 4,520 Home (sqft)
    • 6 Baths
    • 13,068 Lot (sqft)
  13. Photo of 2518 Sweetwater Trail, Winter Park, FL 32789 (MLS # O6255305)
    $654,900
    Photo of 2518 Sweetwater Trail, Winter Park, FL 32789 (MLS # O6255305)
    Photo of 2518 Sweetwater Trail, Winter Park, FL 32789 (MLS # O6255305)
    41
     
    2518 Sweetwater Trail, Winter Park, FL
    2518 Sweetwater Trail
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 2,205 Home (sqft)
    • 2 Baths
    • 11,762 Lot (sqft)
  14. Photo of 640 Worthington Drive, Winter Park, FL 32789 (MLS # O6255730)
    $980,000
    Photo of 640 Worthington Drive, Winter Park, FL 32789 (MLS # O6255730)
    Photo of 640 Worthington Drive, Winter Park, FL 32789 (MLS # O6255730)
    640 Worthington Drive, Winter Park, FL
    640 Worthington Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 2,012 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  15. Photo of 1010 N Pennsylvania Avenue, Winter Park, FL 32789 (MLS # O6254839)
    $2,800,000
    Photo of 1010 N Pennsylvania Avenue, Winter Park, FL 32789 (MLS # O6254839)
    Photo of 1010 N Pennsylvania Avenue, Winter Park, FL 32789 (MLS # O6254839)
    1010 N Pennsylvania Avenue, Winter Park, FL
    1010 N Pennsylvania Avenue
    Winter Park, FL
    • 4 Beds
    • 5 Baths
    • 4,074 Home (sqft)
    • 5 Baths
    • 9,584 Lot (sqft)
  16. Photo of 627 Carvell Drive, Winter Park, FL 32792 (MLS # O6255765)
    $448,800
    Photo of 627 Carvell Drive, Winter Park, FL 32792 (MLS # O6255765)
    Photo of 627 Carvell Drive, Winter Park, FL 32792 (MLS # O6255765)
    627 Carvell Drive, Winter Park, FL
    627 Carvell Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,346 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  17. Photo of 236 Scottsdale Square #236, Winter Park, FL 32792 (MLS # O6255508)
    $139,000
    Photo of 236 Scottsdale Square #236, Winter Park, FL 32792 (MLS # O6255508)
    Photo of 236 Scottsdale Square #236, Winter Park, FL 32792 (MLS # O6255508)
    236 Scottsdale Square #236, Winter Park, FL
    236 Scottsdale Square #236
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,085 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  18. Photo of 7475 Canford Court #21, Winter Park, FL 32792 (MLS # O6253905)
    $250,000
    Photo of 7475 Canford Court #21, Winter Park, FL 32792 (MLS # O6253905)
    Photo of 7475 Canford Court #21, Winter Park, FL 32792 (MLS # O6253905)
    7475 Canford Court #21, Winter Park, FL
    7475 Canford Court #21
    Winter Park, FL
    • 2 Beds
    • 3 Baths
    • 1,611 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  19. Photo of 285 Lewfield Circle #285, Winter Park, FL 32792 (MLS # O6256033)
    $175,000
    Photo of 285 Lewfield Circle #285, Winter Park, FL 32792 (MLS # O6256033)
    Photo of 285 Lewfield Circle #285, Winter Park, FL 32792 (MLS # O6256033)
    285 Lewfield Circle #285, Winter Park, FL
    285 Lewfield Circle #285
    Winter Park, FL
    • 1 Bed
    • 1 Bath
    • 678 Home (sqft)
    • 1 Bath
    • 872 Lot (sqft)
  20. Photo of 512 Byron Road, Winter Park, FL 32792 (MLS # O6255318)
    $450,000
    Photo of 512 Byron Road, Winter Park, FL 32792 (MLS # O6255318)
    Photo of 512 Byron Road, Winter Park, FL 32792 (MLS # O6255318)
    512 Byron Road, Winter Park, FL
    512 Byron Road
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,353 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  21. Photo of 1820 Blaine Terrace, Winter Park, FL 32792 (MLS # O6254945)
    $449,000
    Photo of 1820 Blaine Terrace, Winter Park, FL 32792 (MLS # O6254945)
    Photo of 1820 Blaine Terrace, Winter Park, FL 32792 (MLS # O6254945)
    1820 Blaine Terrace, Winter Park, FL
    1820 Blaine Terrace
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,725 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  22. Photo of 2607 Verde Lane, Winter Park, FL 32792 (MLS # O6253344)
    $400,000
    Photo of 2607 Verde Lane, Winter Park, FL 32792 (MLS # O6253344)
    Photo of 2607 Verde Lane, Winter Park, FL 32792 (MLS # O6253344)
    2607 Verde Lane, Winter Park, FL
    2607 Verde Lane
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,953 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  23. Photo of 1795 Walker Avenue, Winter Park, FL 32789 (MLS # O6254742)
    $969,000
    Photo of 1795 Walker Avenue, Winter Park, FL 32789 (MLS # O6254742)
    Photo of 1795 Walker Avenue, Winter Park, FL 32789 (MLS # O6254742)
    37
     
    1795 Walker Avenue, Winter Park, FL
    1795 Walker Avenue
    Winter Park, FL
    • 5 Beds
    • 3 Baths
    • 1,813 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  24. Photo of 7317 Forest Hill Court #235, Winter Park, FL 32792 (MLS # O6253625)
    $235,000
    Photo of 7317 Forest Hill Court #235, Winter Park, FL 32792 (MLS # O6253625)
    Photo of 7317 Forest Hill Court #235, Winter Park, FL 32792 (MLS # O6253625)
    7317 Forest Hill Court #235, Winter Park, FL
    7317 Forest Hill Court #235
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,117 Home (sqft)
    • 2 Baths
    • 1.66 Lot (ac)
  25. Photo of 3651 N Goldenrod Rd #F210, Winter Park, FL 32792 (MLS # O6254613)
    $189,900
    Photo of 3651 N Goldenrod Rd #F210, Winter Park, FL 32792 (MLS # O6254613)
    Photo of 3651 N Goldenrod Rd #F210, Winter Park, FL 32792 (MLS # O6254613)
    3651 N Goldenrod Rd #F210, Winter Park, FL
    3651 N Goldenrod Rd #F210
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 840 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  26. Photo of 1402 Bessmor Road, Winter Park, FL 32789 (MLS # O6254390)
    $469,900
    Photo of 1402 Bessmor Road, Winter Park, FL 32789 (MLS # O6254390)
    Photo of 1402 Bessmor Road, Winter Park, FL 32789 (MLS # O6254390)
    1402 Bessmor Road, Winter Park, FL
    1402 Bessmor Road
    Winter Park, FL
    • 4 Beds
    • 1 Bath
    • 1,100 Home (sqft)
    • 1 Bath
    • 6,970 Lot (sqft)
  27. Photo of 145 Scottsdale Square #145, Winter Park, FL 32792 (MLS # S5114886)
    $160,000
    Photo of 145 Scottsdale Square #145, Winter Park, FL 32792 (MLS # S5114886)
    Photo of 145 Scottsdale Square #145, Winter Park, FL 32792 (MLS # S5114886)
    145 Scottsdale Square #145, Winter Park, FL
    145 Scottsdale Square #145
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,020 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  28. Photo of 5240 N Lake Burkett Lane, Winter Park, FL 32792 (MLS # O6254524)
    $550,000
    Photo of 5240 N Lake Burkett Lane, Winter Park, FL 32792 (MLS # O6254524)
    Photo of 5240 N Lake Burkett Lane, Winter Park, FL 32792 (MLS # O6254524)
    5240 N Lake Burkett Lane, Winter Park, FL
    5240 N Lake Burkett Lane
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,290 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  29. Photo of 1716 Palmer Avenue, Winter Park, FL 32789 (MLS # TB8316437)
    $1,729,000
    Photo of 1716 Palmer Avenue, Winter Park, FL 32789 (MLS # TB8316437)
    Photo of 1716 Palmer Avenue, Winter Park, FL 32789 (MLS # TB8316437)
    1716 Palmer Avenue, Winter Park, FL
    1716 Palmer Avenue
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 3,270 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
  30. Photo of 1570 Grove Terrace, Winter Park, FL 32789 (MLS # O6253722)
    $750,000
    Photo of 1570 Grove Terrace, Winter Park, FL 32789 (MLS # O6253722)
    Photo of 1570 Grove Terrace, Winter Park, FL 32789 (MLS # O6253722)
    1570 Grove Terrace, Winter Park, FL
    1570 Grove Terrace
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,663 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
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The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 11/23/24 12:13 AM PST.

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